PL129835B1 - Method of manufacture of ester derivatives of cyclopropanecarboxylic acid - Google Patents
Method of manufacture of ester derivatives of cyclopropanecarboxylic acid Download PDFInfo
- Publication number
- PL129835B1 PL129835B1 PL1981230784A PL23078481A PL129835B1 PL 129835 B1 PL129835 B1 PL 129835B1 PL 1981230784 A PL1981230784 A PL 1981230784A PL 23078481 A PL23078481 A PL 23078481A PL 129835 B1 PL129835 B1 PL 129835B1
- Authority
- PL
- Poland
- Prior art keywords
- cis
- isomers
- mixture
- crystallization
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- -1 ester derivatives of cyclopropanecarboxylic acid Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 64
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
- 238000002425 crystallisation Methods 0.000 claims description 41
- 230000008025 crystallization Effects 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 12
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 229940043279 diisopropylamine Drugs 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 33
- 239000007858 starting material Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 229940086542 triethylamine Drugs 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- 238000004811 liquid chromatography Methods 0.000 description 6
- 230000000361 pesticidal effect Effects 0.000 description 6
- 239000005946 Cypermethrin Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 4
- 229960005424 cypermethrin Drugs 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 4
- 230000006340 racemization Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- LLMLSUSAKZVFOA-UHFFFAOYSA-M 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1C([O-])=O LLMLSUSAKZVFOA-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Geophysics And Detection Of Objects (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8013308 | 1980-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL230784A1 PL230784A1 (de) | 1982-02-15 |
| PL129835B1 true PL129835B1 (en) | 1984-06-30 |
Family
ID=10512950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981230784A PL129835B1 (en) | 1980-04-23 | 1981-04-21 | Method of manufacture of ester derivatives of cyclopropanecarboxylic acid |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4427598A (de) |
| JP (1) | JPS56166163A (de) |
| AR (1) | AR247469A1 (de) |
| AT (1) | AT372675B (de) |
| AU (1) | AU536528B2 (de) |
| BE (2) | BE888336A (de) |
| BG (1) | BG35744A3 (de) |
| BR (1) | BR8102377A (de) |
| CA (1) | CA1162560A (de) |
| CH (1) | CH646419A5 (de) |
| CS (1) | CS248016B2 (de) |
| DD (1) | DD158239A5 (de) |
| DE (1) | DE3115881A1 (de) |
| DK (1) | DK157677C (de) |
| EG (1) | EG14923A (de) |
| ES (1) | ES501504A0 (de) |
| FI (1) | FI71728C (de) |
| FR (1) | FR2481274B1 (de) |
| GR (1) | GR74495B (de) |
| HU (1) | HU186407B (de) |
| IE (1) | IE51195B1 (de) |
| IL (1) | IL62685A (de) |
| IN (1) | IN155977B (de) |
| IT (1) | IT1137380B (de) |
| LU (1) | LU83308A1 (de) |
| NL (1) | NL8101937A (de) |
| NO (1) | NO151619C (de) |
| NZ (1) | NZ196881A (de) |
| OA (1) | OA06792A (de) |
| PH (1) | PH18642A (de) |
| PL (1) | PL129835B1 (de) |
| PT (1) | PT72894B (de) |
| RO (1) | RO83587B (de) |
| SE (1) | SE453188B (de) |
| SU (1) | SU1349697A3 (de) |
| TR (1) | TR21337A (de) |
| YU (1) | YU42395B (de) |
| ZA (1) | ZA812595B (de) |
| ZW (1) | ZW8981A1 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1206483A (en) * | 1982-11-11 | 1986-06-24 | Johannes Van Berkel | Process for preparing cyclopropane carboxylic acid ester derivatives |
| DE3401483A1 (de) * | 1984-01-18 | 1985-07-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl-ester |
| CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
| US4997970A (en) * | 1987-06-15 | 1991-03-05 | Fmc Corporation | Conversion of pyrethroid isomers to move active species |
| US5128497A (en) * | 1990-01-03 | 1992-07-07 | Fmc Corporation | Conversion of pyrethroid isomers to more active species |
| GB9127355D0 (en) * | 1991-12-24 | 1992-02-19 | Ici Plc | Isomerisation process |
| GB0229803D0 (en) | 2002-12-20 | 2003-01-29 | Syngenta Ltd | Chemical process |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1413491A (en) | 1972-05-25 | 1975-11-12 | Nat Res Dev | 3-substituted-2,2-dimethyl-cyclopropane carboxylic acid esters their preparation and their use in pesticidal compositions |
| US4024163A (en) | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
| FR2375161A1 (fr) | 1976-04-23 | 1978-07-21 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s) |
| FR2348901A1 (fr) | 1976-04-23 | 1977-11-18 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire alpha-cyane optiquement actif en ester d'acide chiral d'alcool secondaire alpha-cyane racemique |
| FR2383147A2 (fr) * | 1977-03-09 | 1978-10-06 | Roussel Uclaf | Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif en ester d'acide chiral d'alcool secondaire a-cyane racemique |
| US4176195A (en) | 1978-07-20 | 1979-11-27 | Sumitomo Chemical Company, Limited | Pesticidal α-cyanobenzyl ester enantiomer pair |
| US4261921A (en) * | 1979-06-06 | 1981-04-14 | Fmc Corporation | Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair |
| CA1150301A (en) * | 1979-11-27 | 1983-07-19 | Michael J. Bull | Cyclopropane carboxylic acid ester derivatives |
| US4260633A (en) | 1980-04-21 | 1981-04-07 | Zoecon Corporation | Pesticidal esters of amino acids |
-
1981
- 1981-03-10 CA CA000372649A patent/CA1162560A/en not_active Expired
- 1981-04-09 BE BE1/10197A patent/BE888336A/nl not_active IP Right Cessation
- 1981-04-10 US US06/252,891 patent/US4427598A/en not_active Expired - Lifetime
- 1981-04-20 BR BR8102377A patent/BR8102377A/pt not_active IP Right Cessation
- 1981-04-21 CS CS813004A patent/CS248016B2/cs unknown
- 1981-04-21 SE SE8102525A patent/SE453188B/sv not_active IP Right Cessation
- 1981-04-21 ZW ZW89/81A patent/ZW8981A1/xx unknown
- 1981-04-21 ZA ZA00812595A patent/ZA812595B/xx unknown
- 1981-04-21 FI FI811228A patent/FI71728C/fi not_active IP Right Cessation
- 1981-04-21 EG EG223/81A patent/EG14923A/xx active
- 1981-04-21 FR FR8107910A patent/FR2481274B1/fr not_active Expired
- 1981-04-21 NO NO811340A patent/NO151619C/no not_active IP Right Cessation
- 1981-04-21 LU LU83308A patent/LU83308A1/fr unknown
- 1981-04-21 DE DE19813115881 patent/DE3115881A1/de active Granted
- 1981-04-21 JP JP5929281A patent/JPS56166163A/ja active Granted
- 1981-04-21 CH CH259881A patent/CH646419A5/de not_active IP Right Cessation
- 1981-04-21 RO RO104090A patent/RO83587B/ro unknown
- 1981-04-21 DD DD81229361A patent/DD158239A5/de not_active IP Right Cessation
- 1981-04-21 HU HU811030A patent/HU186407B/hu unknown
- 1981-04-21 BG BG051777A patent/BG35744A3/xx unknown
- 1981-04-21 DK DK178281A patent/DK157677C/da active
- 1981-04-21 IL IL62685A patent/IL62685A/xx not_active IP Right Cessation
- 1981-04-21 PT PT72894A patent/PT72894B/pt unknown
- 1981-04-21 SU SU813275450A patent/SU1349697A3/ru active
- 1981-04-21 AT AT0179581A patent/AT372675B/de not_active IP Right Cessation
- 1981-04-21 GR GR64755A patent/GR74495B/el unknown
- 1981-04-21 YU YU1050/81A patent/YU42395B/xx unknown
- 1981-04-21 ES ES501504A patent/ES501504A0/es active Granted
- 1981-04-21 IT IT21308/81A patent/IT1137380B/it active
- 1981-04-21 AR AR81285023A patent/AR247469A1/es active
- 1981-04-21 AU AU69675/81A patent/AU536528B2/en not_active Expired
- 1981-04-21 IN IN243/DEL/81A patent/IN155977B/en unknown
- 1981-04-21 OA OA57382A patent/OA06792A/xx unknown
- 1981-04-21 TR TR21337A patent/TR21337A/xx unknown
- 1981-04-21 NL NL8101937A patent/NL8101937A/nl active Search and Examination
- 1981-04-21 PH PH25524A patent/PH18642A/en unknown
- 1981-04-21 PL PL1981230784A patent/PL129835B1/pl unknown
- 1981-04-22 IE IE897/81A patent/IE51195B1/en not_active IP Right Cessation
- 1981-04-22 NZ NZ196881A patent/NZ196881A/xx unknown
-
1983
- 1983-07-28 BE BE1/10841A patent/BE897395A/nl not_active IP Right Cessation
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